2,6,10-Trimethyl-dodeca-4,8-dien-1-al → 2,6,10-Trimethyl-dodecan-1-al

HRID 1414463Notes

Reaction equation

HRID 1414463 reaction equation
[CH3:1][CH:2]([CH2:5][CH:6]=[CH:7][CH:8]([CH3:16])[CH2:9][CH:10]=[CH:11][CH:12]([CH3:15])[CH2:13][CH3:14])[CH:3]=[O:4]>O1CCCC1.[Pd]>[CH3:1][CH:2]([CH2:5][CH2:6][CH2:7][CH:8]([CH3:16])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:15])[CH2:13][CH3:14])[CH:3]=[O:4]

Participants

4

Reactant 1

HCID 543547842,6,10-Trimethyl-dodeca-4,8-dien-1-al

Product 1

HCID 189566932,6,10-Trimethyl-dodecan-1-alYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

22 g (0.1 mole) of 2,6,10-trimethyl-dodeca-4,8-dien-1-al are dissolved in 20 ml of tetrahydrofuran, 1 g of a palladium/charcoal catalyst (1%) is added and hydrogenation is carried out at 70° C until the absorption of hydrogen has ceased. The catalyst is then filtered off, the solvent distilled off and the residue is fractionated through a descending condenser. 21 g of 2,6,10-trimethyl-dodecan-1-al are obtained (yield, 93% of theory). B.p. = 80° - 81° C at 0.3 mm Hg; nD25 = 1.4456. Odor: bitter, greener and more aldehyde-like orange scent.

Workup

  1. customhydrogenation is carried out at 70° C until the absorption of hydrogen
  2. filtrationThe catalyst is then filtered off
  3. distillationthe solvent distilled off
  4. customthe residue is fractionated through a descending condenser

Sources & evidence

ORD record
ord-488f29d7f5754b8fab0ceaf172aea2f3
Source dataset
uspto-grants-1977_01
Patent number
US04001336

Reaction notes

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